US4942173A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pesticidal compounds
Assignee: Sanofi Aventis France
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Filing: 1989-02-24
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Granted: 1990-07-17
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Expires: 2009-02-24
Abstract
Abstract The present invention relates to a compound of the formula (I): <IMAGE> (I) wherein R is C2-10 alkyl, alkenyl or alkynyl, each optionally substituted by or methyl substituted by cyano, C3-4 cycloalkyl, halo, C1-4 alkoxy or a group S(O)m R4 where R4 is C1-4 alkyl and m is 0, 1 or 2, or Ris C3-10 cycloalkyl, C4-10 cycloalkenyl or phenyl, each optionally substituted by C1-4 alkoxy, C1-3 alkyl, C2-4 alkynyl, halo, cyano or a group S(O)m R4 as defined hereinbefore; R1 is halo, C1-3 alkyl, C2-3 alkenyl or alkynyl each optionally substituted by halo, cyano, C1-4 alkoxy, alkyl carbalkoxy containing up to 6 carbon atoms, a group S(O)m R4 as defined hereinbefore or alkynyl substituted by tri-C1-4 alkylsilyl, or R1 is cyano, spiro-cyclopropyl, gem dimethyl, gem dicyano, gem diethynyl, oxo or methylene optionally substituted by cyano of C1-3 alkyl optionally substituted by fluorine, or R1 and R and the carbon atoms to which they are attached form a C5-7 carbocyclic ring optionally substituted by halo, C1-3 alkyl or alkoxy or C2-3 alkenyl, R2 is phenyl substituted by an C2-3 alkynyl group or by a tri-C1-4 alkylsilylalkynyl group and R3 is hydrogen, C1-3 alkyl, C2-3 alkenyl or alkynyl each optionally substituted by cyano, C1-4 alkylthio, C1-4 alkoxy or halo, or R3 is cyano or halo, its use in medicine, pharmaceutical compositions containing it and its preparation.
Inventors
- 👤 John E. Casida
- 👤 Christopher J. Palmer
- 👤 John P. Larkin
- 👤 Ian H. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 04:30
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08; A; A01; A01N; A01N43/00; A01N43/90; A01N55/00; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/04; C07C43/13; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
242 words
A compound of the formula (I): ##STR12## wherein R is C 2-10 alkyl, alkenyl or alkynyl, each optionally substituted by or methyl substituted by cyano, C 3-4 cycloalkyl, halo, C 1-4 alkoxy or a group S(O)m R 4 where R 4 is C 1-4 alkyl and m is 0, 1 or 2, or R is C 3-10 cycloalkyl, C 4-10 cycloalkenyl or phenyl, each optionally substituted by C 1-4 alkoxy, C 1-3 alkyl, C 2-4 alkynyl, halo, cyano or a group S(O)m R 4 as defined hereinbefore; R 1 is halo, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by halo, cyano, C 1-4 alkoxy, alkyl carbalkoxy containing up to 6 carbon atoms, a group S(O)m R 4 as defined hereinbefore or alkynyl substituted by tri-C 1-4 alkylsilyl, or R 1 is cyano, spirocyclopropyl, gem dimethyl, gem dicyano, gem diethynyl, oxo or methylene optionally substituted by cyano or C 1-3 alkyl optionally substituted by fluorine, or R 1 and R and the carbon atoms to which they are attached form a C 5-7 carbocyclic ring optionally substituted by halo, C 1-3 alkyl or alkoxy or C 2-3 alkenyl, R 2 is phenyl substituted by an C 2-3 alkynyl group or by a tri-C 1-4 alkylsilylalkynyl group and R 3 is hydrogen, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkylthio, C 1-4 alkoxy or halo, or R 3 is cyano or halo.
Claim 2
Dependent Claim
242 words
A compound of the formula (I): ##STR12## wherein R is C 2-10 alkyl, alkenyl or alkynyl, each optionally substituted by or methyl substituted by cyano, C 3-4 cycloalkyl, halo, C 1-4 alkoxy or a group S(O)m R 4 where R 4 is C 1-4 alkyl and m is 0, 1 or 2, or R is C 3-10 cycloalkyl, C 4-10 cycloalkenyl or phenyl, each optionally substituted by C 1-4 alkoxy, C 1-3 alkyl, C 2-4 alkynyl, halo, cyano or a group S(O)m R 4 as defined hereinbefore; R 1 is halo, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by halo, cyano, C 1-4 alkoxy, alkyl carbalkoxy containing up to 6 carbon atoms, a group S(O)m R 4 as defined hereinbefore or alkynyl substituted by tri-C 1-4 alkylsilyl, or R 1 is cyano, spirocyclopropyl, gem dimethyl, gem dicyano, gem diethynyl, oxo or methylene optionally substituted by cyano or C 1-3 alkyl optionally substituted by fluorine, or R 1 and R and the carbon atoms to which they are attached form a C 5-7 carbocyclic ring optionally substituted by halo, C 1-3 alkyl or alkoxy or C 2-3 alkenyl, R 2 is phenyl substituted by an C 2-3 alkynyl group or by a tri-C 1-4 alkylsilylalkynyl group and R 3 is hydrogen, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkylthio, C 1-4 alkoxy or halo, or R 3 is cyano or halo.
Claim 3
Dependent Claim
18 words
A compound according to claim 1 in which R is n-propyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclopentyl or cyclohexyl.
Claim 4
Dependent Claim
16 words
A compound according to claim 1 which R 1 is methyl, ethyl, trifluoromethyl, cyano or ethynyl.
Claim 5
Dependent Claim
14 words
A compound according to claim 1 in which R 3 is hydrogen or methyl.
Claim 6
Dependent Claim
130 words
A compound of the formula IA: ##STR13## wherein R a is C 2-4 alkyl, alkenyl or alkynyl, C 5-10 cycloalkyl or phenyl, each optionally substituted by cyano or C 1-4 alkoxy, R 1a is cyano or C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkoxy, C 1-4 alkylthio or halo, or R 1a is cyano, gem dimethyl or R 1a and R a and the carbon atoms to which they are attached form a C 5-7 carbocyclic ring optionally substituted by C 1-3 alkyl or alkoxy; R 2a is phenyl, substituted by an C 2-3 alkynyl group and R 3a is hydrogen, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkylthio, C 1-4 alkoxy or halo.
Claim 7
Dependent Claim
130 words
A compound of the formula IA: ##STR13## wherein R a is C 2-4 alkyl, alkenyl or alkynyl, C 5-10 cycloalkyl or phenyl, each optionally substituted by cyano or C 1-4 alkoxy, R 1a is cyano or C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkoxy, C 1-4 alkylthio or halo, or R 1a is cyano, gem dimethyl or R 1a and R a and the carbon atoms to which they are attached form a C 5-7 carbocyclic ring optionally substituted by C 1-3 alkyl or alkoxy; R 2a is phenyl, substituted by an C 2-3 alkynyl group and R 3a is hydrogen, C 1-3 alkyl, C 2-3 alkenyl or alkynyl each optionally substituted by cyano, C 1-4 alkylthio, C 1-4 alkoxy or halo.
Claim 8
Dependent Claim
15 words
A compound selected from: 1-(4-ethynylphenyl)-3-methyl-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 3-methyl-4-n-propyl-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo-[2,2,2]octane, 1-(4-ethynylphenyl)-4-n-propyl-3-trifluoromethyl-2,6,7-trioxabicyclo[2,2,2]octane, 4-n-propyl-3-trifluoromethyl-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo[2,2,2]octane, 3-cyano-1-(4-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 4-t-butyl-3-cyano-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2,2,2]octane, 4-t-butyl-3-cyano-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo[2,2,2]octane, 4-n-Butyl-3-methyl-1-[4-(2-trimethylsilylethynyl)phenyl]-2,6,7-trioxabicyclo[2,2,2octane, 4-n-Butyl-1-(4-ethynylphenyl)-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane, 3-Cyano-4-n-propyl-1-[4-(2-trimethylsilylethynyl)phenyl]-2,6,7-trioxabicyclo[2,2,2octane, 3-Cyano-1-(4-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane.
Claim 9
Dependent Claim
15 words
A compound selected from: 1-(4-ethynylphenyl)-3-methyl-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 3-methyl-4-n-propyl-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo-[2,2,2]octane, 1-(4-ethynylphenyl)-4-n-propyl-3-trifluoromethyl-2,6,7-trioxabicyclo[2,2,2]octane, 4-n-propyl-3-trifluoromethyl-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo[2,2,2]octane, 3-cyano-1-(4-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane, 4-t-butyl-3-cyano-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2,2,2]octane, 4-t-butyl-3-cyano-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo[2,2,2]octane, 4-n-Butyl-3-methyl-1-[4-(2-trimethylsilylethynyl)phenyl]-2,6,7-trioxabicyclo[2,2,2octane, 4-n-Butyl-1-(4-ethynylphenyl)-3-methyl-2,6,7-trioxabicyclo[2,2,2]octane, 3-Cyano-4-n-propyl-1-[4-(2-trimethylsilylethynyl)phenyl]-2,6,7-trioxabicyclo[2,2,2octane, 3-Cyano-1-(4-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo[2,2,2]octane.
Claim 10
Dependent Claim
18 words
An insecticidal or acaricidal composition comprising a compound of formula (I) in admixture with a carrier or diluent.
Claim 11
Dependent Claim
18 words
An insecticidal or acaricidal composition comprising a compound of formula (I) in admixture with a carrier or diluent.
Claim 12
Dependent Claim
24 words
A synergized pesticidal composition comprising a compound of formula (I) together with a oxidase inhibitor or potentiator for the pesticidal compound of formula (I).
Claim 13
Dependent Claim
24 words
A synergized pesticidal composition comprising a compound of formula (I) together with a oxidase inhibitor or potentiator for the pesticidal compound of formula (I).
Claim 14
Independent Claim
23 words
A method for the control of arthropod pests comprising the application to the pest or its environment of a compound of formula (I).
Claim 15
Independent Claim
23 words
A method for the control of arthropod pests comprising the application to the pest or its environment of a compound of formula (I).
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-07-16 | 1994-01-15 | 1994-07-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-07-16 | 1998-01-15 | 1998-07-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-07-16 | 2002-01-15 | 2002-07-17 | $7700.00 | Window Closed / Lapsed |